JP5053492B2 - Ｂａｘ修飾物質としての９−（ピペラジニルアルキル）カルバゾール - Google Patents

Ｂａｘ修飾物質としての９−（ピペラジニルアルキル）カルバゾール Download PDF

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Publication number: JP5053492B2
Authority: JP; Japan
Prior art keywords: piperazin; propan; carbazol; dibromocarbazol; substituted
Prior art date: 1999-10-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

JP2001531827A

Other languages

English (en)

Japanese (ja)

Other versions

JP2003512371A (ja

Inventor

アラジイ，セルジュ

チャーチ，デニス

アントンソン，ブルーノ

ボンブリュン，アニェ

ジェルベール，パトリック

マルティノー，ジャン−クロード

Original Assignee

メルクセローノソシエテアノニム

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-10-18

Filing date

2000-10-18

Publication date

2012-10-17

2000-10-18 Application filed by メルクセローノソシエテアノニム filed Critical メルクセローノソシエテアノニム

2003-04-02 Publication of JP2003512371A publication Critical patent/JP2003512371A/ja

2012-10-17 Application granted granted Critical

2012-10-17 Publication of JP5053492B2 publication Critical patent/JP5053492B2/ja

2020-10-18 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 80
239000003607 modifier Substances 0.000 title description 2
150000004885 piperazines Chemical class 0.000 claims abstract description 44
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 claims abstract description 18
-1 Aminokaruboni Chemical group 0.000 claims description 200
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 47
125000003118 aryl group Chemical group 0.000 claims description 42
239000001257 hydrogen Substances 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 34
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 31
229910052736 halogen Inorganic materials 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 30
125000001072 heteroaryl group Chemical group 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 23
238000004519 manufacturing process Methods 0.000 claims description 21
MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
XLYZLUUJTCDDDV-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(furan-2-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=CO1 XLYZLUUJTCDDDV-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
GUAFOGOEJLSQBT-UHFFFAOYSA-N scoparone Chemical compound C1=CC(=O)OC2=C1C=C(OC)C(OC)=C2 GUAFOGOEJLSQBT-UHFFFAOYSA-N 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
PCWZKCYVZREDJQ-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-(thiophen-3-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC=1C=CSC=1 PCWZKCYVZREDJQ-UHFFFAOYSA-N 0.000 claims description 5
IOYOOVIEADEXNK-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(F)C=C1 IOYOOVIEADEXNK-UHFFFAOYSA-N 0.000 claims description 5
IQGSRHMTIXSIET-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C1=CC(OC)=CC=C1CN1CCN(CC(O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)CC1 IQGSRHMTIXSIET-UHFFFAOYSA-N 0.000 claims description 5
PNRFIADJLMAJLG-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-piperazin-1-ylpropan-2-one Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(=O)CN1CCNCC1 PNRFIADJLMAJLG-UHFFFAOYSA-N 0.000 claims description 5
JLNUOTRGJFMVLN-UHFFFAOYSA-N 1-(3-phenylcarbazol-9-yl)-3-piperazin-1-ylpropan-2-ol Chemical compound C12=CC=CC=C2C2=CC(C=3C=CC=CC=3)=CC=C2N1CC(O)CN1CCNCC1 JLNUOTRGJFMVLN-UHFFFAOYSA-N 0.000 claims description 5
125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
KUUJEXLRLIPQQJ-UHFFFAOYSA-N 1-(3,6-dibromo-9-carbazolyl)-3-(1-piperazinyl)-2-propanol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCNCC1 KUUJEXLRLIPQQJ-UHFFFAOYSA-N 0.000 claims description 4
YNZMVOHVKCATSX-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-piperazin-1-ylpropan-2-amine Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(N)CN1CCNCC1 YNZMVOHVKCATSX-UHFFFAOYSA-N 0.000 claims description 4
MUTYIBZJFUUPAA-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=CC=C1 MUTYIBZJFUUPAA-UHFFFAOYSA-N 0.000 claims description 4
XKOVUBDUNUHXSO-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-3-carbazol-9-ylpropan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=CC=C1 XKOVUBDUNUHXSO-UHFFFAOYSA-N 0.000 claims description 4
NJLXIBFLHGNMIT-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-(3-bromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCN(CC=2C=C3OCOC3=CC=2)CC1 NJLXIBFLHGNMIT-UHFFFAOYSA-N 0.000 claims description 4
WATOFYBPVZCCCL-UHFFFAOYSA-N 1-carbazol-9-yl-3-piperazin-1-ylpropan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN1CCNCC1 WATOFYBPVZCCCL-UHFFFAOYSA-N 0.000 claims description 4
RUTWJFHUJLHOGI-UHFFFAOYSA-N [4-(3-carbazol-9-yl-2-hydroxypropyl)piperazin-1-yl]-phenylmethanone Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1C(=O)C1=CC=CC=C1 RUTWJFHUJLHOGI-UHFFFAOYSA-N 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
INCXSFGDBMWQOM-UHFFFAOYSA-N tert-butyl 4-[2-amino-3-(3,6-dibromocarbazol-9-yl)propyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(N)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 INCXSFGDBMWQOM-UHFFFAOYSA-N 0.000 claims description 4
FFVDXFXAZIAUIN-UHFFFAOYSA-N tert-butyl 4-[3-(3,6-dibromocarbazol-9-yl)-2-oxopropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(=O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 FFVDXFXAZIAUIN-UHFFFAOYSA-N 0.000 claims description 4
HLZOPMNORNCHBF-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(4-thiophen-2-ylsulfonylpiperazin-1-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1S(=O)(=O)C1=CC=CS1 HLZOPMNORNCHBF-UHFFFAOYSA-N 0.000 claims description 3
AEERGXMKSLNULK-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[2-(4-fluorophenyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCNCC1C1=CC=C(F)C=C1 AEERGXMKSLNULK-UHFFFAOYSA-N 0.000 claims description 3
FSBUYKKZNYSJOU-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1C(SN=1)=NC=1C1=CC=CC=C1 FSBUYKKZNYSJOU-UHFFFAOYSA-N 0.000 claims description 3
ITQUVMNKSIBJOS-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-(3-phenylpropyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CCCC1=CC=CC=C1 ITQUVMNKSIBJOS-UHFFFAOYSA-N 0.000 claims description 3
FENVTMZMZGLVQP-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-(4-nitro-2,1,3-benzoxadiazol-7-yl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCN(C=2C3=NON=C3C([N+]([O-])=O)=CC=2)CC1 FENVTMZMZGLVQP-UHFFFAOYSA-N 0.000 claims description 3
NXOPNPSNKVSFRK-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=CN=C1 NXOPNPSNKVSFRK-UHFFFAOYSA-N 0.000 claims description 3
JUEUQCVHANVHHN-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-(thiophen-2-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=CS1 JUEUQCVHANVHHN-UHFFFAOYSA-N 0.000 claims description 3
YHWANUDGXWVPKO-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(Cl)C(Cl)=C1 YHWANUDGXWVPKO-UHFFFAOYSA-N 0.000 claims description 3
QKWCHBPWHPRYLM-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-[[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(C(F)(F)F)C=C1 QKWCHBPWHPRYLM-UHFFFAOYSA-N 0.000 claims description 3
ZVVYKHUGTLYZET-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(2-phenylethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CCC1=CC=CC=C1 ZVVYKHUGTLYZET-UHFFFAOYSA-N 0.000 claims description 3
OPCOCGHIMLNYHL-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(cyclohexylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1CCCCC1 OPCOCGHIMLNYHL-UHFFFAOYSA-N 0.000 claims description 3
LBYZWLYFNYOTBG-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(naphthalen-1-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCN(CC=2C3=CC=CC=C3C=CC=2)CC1 LBYZWLYFNYOTBG-UHFFFAOYSA-N 0.000 claims description 3
DAIXPYZSIGYIFR-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(pyridin-2-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=CC=N1 DAIXPYZSIGYIFR-UHFFFAOYSA-N 0.000 claims description 3
DWHPWKQDSSVZOQ-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(pyridin-3-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=CN=C1 DWHPWKQDSSVZOQ-UHFFFAOYSA-N 0.000 claims description 3
NUDYJBVMNPIWMW-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(pyridin-4-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=NC=C1 NUDYJBVMNPIWMW-UHFFFAOYSA-N 0.000 claims description 3
NKZVNKOIHNFFID-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(quinolin-2-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCN(CC=2N=C3C=CC=CC3=CC=2)CC1 NKZVNKOIHNFFID-UHFFFAOYSA-N 0.000 claims description 3
ONRWTLHWIROPFP-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(quinolin-4-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCN(CC=2C3=CC=CC=C3N=CC=2)CC1 ONRWTLHWIROPFP-UHFFFAOYSA-N 0.000 claims description 3
BYZBYNPYRCAMHE-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(Cl)C(Cl)=C1 BYZBYNPYRCAMHE-UHFFFAOYSA-N 0.000 claims description 3
BOGGGRKNFJMMRT-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-[(3,5-dichlorophenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC(Cl)=CC(Cl)=C1 BOGGGRKNFJMMRT-UHFFFAOYSA-N 0.000 claims description 3
OVZVVMJLKNKWJM-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(F)C=C1 OVZVVMJLKNKWJM-UHFFFAOYSA-N 0.000 claims description 3
ZWIAENIAVASCTF-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C1=CC(OC)=CC=C1CN1CCN(CC(O)CN2C3=CC=C(Br)C=C3C3=CC=CC=C32)CC1 ZWIAENIAVASCTF-UHFFFAOYSA-N 0.000 claims description 3
CNBVTMXKEOUDJW-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-[(4-tert-butylphenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1CCN(CC(O)CN2C3=CC=C(Br)C=C3C3=CC=CC=C32)CC1 CNBVTMXKEOUDJW-UHFFFAOYSA-N 0.000 claims description 3
JWWKFERGBCDVTA-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-[(6-chloro-1,3-benzodioxol-5-yl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCN(CC=2C(=CC=3OCOC=3C=2)Cl)CC1 JWWKFERGBCDVTA-UHFFFAOYSA-N 0.000 claims description 3
SXRXBVIOUFDQMI-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-[[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(C(F)(F)F)C=C1 SXRXBVIOUFDQMI-UHFFFAOYSA-N 0.000 claims description 3
XVXPAKUWKWBDDA-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-piperazin-1-ylpropan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCNCC1 XVXPAKUWKWBDDA-UHFFFAOYSA-N 0.000 claims description 3
WKOYXGMFLMBTJF-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-3-(2-methylcarbazol-9-yl)propan-2-ol Chemical compound C=1C(C)=CC=C(C2=CC=CC=C22)C=1N2CC(O)CN(CC1)CCN1CC1=CC=CC=C1 WKOYXGMFLMBTJF-UHFFFAOYSA-N 0.000 claims description 3
CGZVOZKNJDMXLI-UHFFFAOYSA-N 1-(4-benzylsulfonylpiperazin-1-yl)-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1S(=O)(=O)CC1=CC=CC=C1 CGZVOZKNJDMXLI-UHFFFAOYSA-N 0.000 claims description 3
CWCWUHOHXQZVEJ-UHFFFAOYSA-N 1-(4-butylpiperazin-1-yl)-3-carbazol-9-ylpropan-2-ol Chemical compound C1CN(CCCC)CCN1CC(O)CN1C2=CC=CC=C2C2=CC=CC=C21 CWCWUHOHXQZVEJ-UHFFFAOYSA-N 0.000 claims description 3
MHVDPFCDXYQFNF-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCN(CC=2C=C3OCOC3=CC=2)CC1 MHVDPFCDXYQFNF-UHFFFAOYSA-N 0.000 claims description 3
BEEYWEVWHRDCGG-UHFFFAOYSA-N 1-[4-(3-carbazol-9-yl-2-hydroxypropyl)piperazin-1-yl]-2-(4-hydroxyphenoxy)ethanone Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1C(=O)COC1=CC=C(O)C=C1 BEEYWEVWHRDCGG-UHFFFAOYSA-N 0.000 claims description 3
YNMKUROILLLLNK-UHFFFAOYSA-N 1-[4-(3-carbazol-9-yl-2-hydroxypropyl)piperazin-1-yl]-2-phenoxyethanone Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1C(=O)COC1=CC=CC=C1 YNMKUROILLLLNK-UHFFFAOYSA-N 0.000 claims description 3
CZVHACMAYGICOM-UHFFFAOYSA-N 1-[4-(benzenesulfonyl)piperazin-1-yl]-3-carbazol-9-ylpropan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 CZVHACMAYGICOM-UHFFFAOYSA-N 0.000 claims description 3
LVASKTQPZILVQT-UHFFFAOYSA-N 1-[4-(cyclohexylmethyl)piperazin-1-yl]-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1CCCCC1 LVASKTQPZILVQT-UHFFFAOYSA-N 0.000 claims description 3
JYOXDZBIZWSURJ-UHFFFAOYSA-N 1-[4-(cyclohexylmethyl)piperazin-1-yl]-3-(3,6-dibromocarbazol-9-yl)propan-2-one Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(=O)CN(CC1)CCN1CC1CCCCC1 JYOXDZBIZWSURJ-UHFFFAOYSA-N 0.000 claims description 3
BLRYYFOOBONSDW-UHFFFAOYSA-N 1-[4-(cyclohexylmethyl)piperazin-1-yl]-3-(3-phenylcarbazol-9-yl)propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(C=3C=CC=CC=3)=CC=C2N1CC(O)CN(CC1)CCN1CC1CCCCC1 BLRYYFOOBONSDW-UHFFFAOYSA-N 0.000 claims description 3
KNRCDLZBIYMKLG-UHFFFAOYSA-N 1-[4-(cyclohexylmethyl)piperazin-1-yl]-3-(3-phenylcarbazol-9-yl)propan-2-one Chemical compound C12=CC=CC=C2C2=CC(C=3C=CC=CC=3)=CC=C2N1CC(=O)CN(CC1)CCN1CC1CCCCC1 KNRCDLZBIYMKLG-UHFFFAOYSA-N 0.000 claims description 3
KBNGRILLWNWDIM-UHFFFAOYSA-N 1-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-(3-phenylcarbazol-9-yl)propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(C=3C=CC=CC=3)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(F)C=C1 KBNGRILLWNWDIM-UHFFFAOYSA-N 0.000 claims description 3
RLNQYSKCKFKXJS-UHFFFAOYSA-N 1-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-(3-thiophen-2-ylcarbazol-9-yl)propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(C=3SC=CC=3)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(F)C=C1 RLNQYSKCKFKXJS-UHFFFAOYSA-N 0.000 claims description 3
ZQSXWERSVLEILQ-UHFFFAOYSA-N 1-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-[3-[4-(trifluoromethoxy)phenyl]carbazol-9-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(F)C=C1 ZQSXWERSVLEILQ-UHFFFAOYSA-N 0.000 claims description 3
LSPBYQHEWSOKMM-UHFFFAOYSA-N 1-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]-3-[3-[4-(trifluoromethyl)phenyl]carbazol-9-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(F)C=C1 LSPBYQHEWSOKMM-UHFFFAOYSA-N 0.000 claims description 3
QOKZIHBFWXEMJQ-UHFFFAOYSA-N 1-[4-[(4-tert-butylphenyl)methyl]piperazin-1-yl]-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1CCN(CC(O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)CC1 QOKZIHBFWXEMJQ-UHFFFAOYSA-N 0.000 claims description 3
SLAOUROMKSNUPZ-UHFFFAOYSA-N 1-[4-[(4-tert-butylphenyl)methyl]piperazin-1-yl]-3-carbazol-9-ylpropan-2-ol Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1CCN(CC(O)CN2C3=CC=CC=C3C3=CC=CC=C32)CC1 SLAOUROMKSNUPZ-UHFFFAOYSA-N 0.000 claims description 3
DGFLLGXEHLFXFR-UHFFFAOYSA-N 1-[4-[(6-bromo-1,3-benzodioxol-5-yl)methyl]piperazin-1-yl]-3-(3-bromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN1CCN(CC=2C(=CC=3OCOC=3C=2)Br)CC1 DGFLLGXEHLFXFR-UHFFFAOYSA-N 0.000 claims description 3
VOIDYPPBGZRJMW-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-(3-phenylpropyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1CCCC1=CC=CC=C1 VOIDYPPBGZRJMW-UHFFFAOYSA-N 0.000 claims description 3
YMPLPBKLGFMOSB-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-(thiophen-2-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=CS1 YMPLPBKLGFMOSB-UHFFFAOYSA-N 0.000 claims description 3
PWHPYBTYICXHPI-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-[(3-fluorophenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=CC(F)=C1 PWHPYBTYICXHPI-UHFFFAOYSA-N 0.000 claims description 3
YFBVTWYNQIBJDW-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(F)C=C1 YFBVTWYNQIBJDW-UHFFFAOYSA-N 0.000 claims description 3
WXIZYRMWFYFBOF-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C1=CC(OC)=CC=C1CN1CCN(CC(O)CN2C3=CC=CC=C3C3=CC=CC=C32)CC1 WXIZYRMWFYFBOF-UHFFFAOYSA-N 0.000 claims description 3
ZVMJFECKIRBHNT-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-[(4-methylsulfonylphenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CCN(CC(O)CN2C3=CC=CC=C3C3=CC=CC=C32)CC1 ZVMJFECKIRBHNT-UHFFFAOYSA-N 0.000 claims description 3
PXQUWXHEXADSLK-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-[(4-nitrophenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C([N+]([O-])=O)C=C1 PXQUWXHEXADSLK-UHFFFAOYSA-N 0.000 claims description 3
BZWAEBNONWBNFC-UHFFFAOYSA-N 2-[4-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazin-1-yl]-1-morpholin-4-ylethanone Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC(=O)N1CCOCC1 BZWAEBNONWBNFC-UHFFFAOYSA-N 0.000 claims description 3
XDKXOLMRFOXRNM-UHFFFAOYSA-N 3,6-dibromo-9-(2,2-difluoro-3-piperazin-1-ylpropyl)carbazole Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(F)(F)CN1CCNCC1 XDKXOLMRFOXRNM-UHFFFAOYSA-N 0.000 claims description 3
NKXAXNIFEWPPLX-UHFFFAOYSA-N 9-(2-hydroxy-3-piperazin-1-ylpropyl)carbazole-3,6-dicarbonitrile Chemical compound C12=CC=C(C#N)C=C2C2=CC(C#N)=CC=C2N1CC(O)CN1CCNCC1 NKXAXNIFEWPPLX-UHFFFAOYSA-N 0.000 claims description 3
CDIBTQWFTVIRMH-UHFFFAOYSA-N [4-(3-carbazol-9-yl-2-hydroxypropyl)piperazin-1-yl]-(4-fluorophenyl)methanone Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1C(=O)C1=CC=C(F)C=C1 CDIBTQWFTVIRMH-UHFFFAOYSA-N 0.000 claims description 3
DJLRPKXUQOSFDX-UHFFFAOYSA-N [4-(3-carbazol-9-yl-2-hydroxypropyl)piperazin-1-yl]-(4-hydroxyphenyl)methanone Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1C(=O)C1=CC=C(O)C=C1 DJLRPKXUQOSFDX-UHFFFAOYSA-N 0.000 claims description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
BHOTVLROLWDPES-UHFFFAOYSA-N n-[9-(2-hydroxy-3-piperazin-1-ylpropyl)carbazol-3-yl]acetamide Chemical compound C12=CC=CC=C2C2=CC(NC(=O)C)=CC=C2N1CC(O)CN1CCNCC1 BHOTVLROLWDPES-UHFFFAOYSA-N 0.000 claims description 3
QJMRCCOOANCYQU-UHFFFAOYSA-N tert-butyl 4-(3-carbazol-9-yl-2-hydroxypropyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(O)CN1C2=CC=CC=C2C2=CC=CC=C21 QJMRCCOOANCYQU-UHFFFAOYSA-N 0.000 claims description 3
QURQMIHUXXYJIT-GOSISDBHSA-N tert-butyl 4-[(2r)-3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C[C@@H](O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 QURQMIHUXXYJIT-GOSISDBHSA-N 0.000 claims description 3
RIHAVYINBMLQHZ-GOSISDBHSA-N tert-butyl 4-[(2r)-3-(3-bromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C[C@@H](O)CN1C2=CC=C(Br)C=C2C2=CC=CC=C21 RIHAVYINBMLQHZ-GOSISDBHSA-N 0.000 claims description 3
RIHAVYINBMLQHZ-SFHVURJKSA-N tert-butyl 4-[(2s)-3-(3-bromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C[C@H](O)CN1C2=CC=C(Br)C=C2C2=CC=CC=C21 RIHAVYINBMLQHZ-SFHVURJKSA-N 0.000 claims description 3
QURQMIHUXXYJIT-UHFFFAOYSA-N tert-butyl 4-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 QURQMIHUXXYJIT-UHFFFAOYSA-N 0.000 claims description 3
PCWZKCYVZREDJQ-HXUWFJFHSA-N (2r)-1-(3,6-dibromocarbazol-9-yl)-3-[4-(thiophen-3-ylmethyl)piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21)N(CC1)CCN1CC=1C=CSC=1 PCWZKCYVZREDJQ-HXUWFJFHSA-N 0.000 claims description 2
IOYOOVIEADEXNK-JOCHJYFZSA-N (2r)-1-(3,6-dibromocarbazol-9-yl)-3-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21)N(CC1)CCN1CC1=CC=C(F)C=C1 IOYOOVIEADEXNK-JOCHJYFZSA-N 0.000 claims description 2
IQGSRHMTIXSIET-JOCHJYFZSA-N (2r)-1-(3,6-dibromocarbazol-9-yl)-3-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C1=CC(OC)=CC=C1CN1CCN(C[C@@H](O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)CC1 IQGSRHMTIXSIET-JOCHJYFZSA-N 0.000 claims description 2
YNZMVOHVKCATSX-OAHLLOKOSA-N (2r)-1-(3,6-dibromocarbazol-9-yl)-3-piperazin-1-ylpropan-2-amine Chemical compound C([C@@H](N)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21)N1CCNCC1 YNZMVOHVKCATSX-OAHLLOKOSA-N 0.000 claims description 2
JLNUOTRGJFMVLN-OAQYLSRUSA-N (2r)-1-(3-phenylcarbazol-9-yl)-3-piperazin-1-ylpropan-2-ol Chemical compound C([C@@H](O)CN1C2=CC=C(C=C2C2=CC=CC=C21)C=1C=CC=CC=1)N1CCNCC1 JLNUOTRGJFMVLN-OAQYLSRUSA-N 0.000 claims description 2
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IQGSRHMTIXSIET-QFIPXVFZSA-N (2s)-1-(3,6-dibromocarbazol-9-yl)-3-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C1=CC(OC)=CC=C1CN1CCN(C[C@H](O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)CC1 IQGSRHMTIXSIET-QFIPXVFZSA-N 0.000 claims description 2
YNZMVOHVKCATSX-HNNXBMFYSA-N (2s)-1-(3,6-dibromocarbazol-9-yl)-3-piperazin-1-ylpropan-2-amine Chemical compound C([C@H](N)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21)N1CCNCC1 YNZMVOHVKCATSX-HNNXBMFYSA-N 0.000 claims description 2
JLNUOTRGJFMVLN-NRFANRHFSA-N (2s)-1-(3-phenylcarbazol-9-yl)-3-piperazin-1-ylpropan-2-ol Chemical compound C([C@H](O)CN1C2=CC=C(C=C2C2=CC=CC=C21)C=1C=CC=CC=1)N1CCNCC1 JLNUOTRGJFMVLN-NRFANRHFSA-N 0.000 claims description 2
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HENAKKLFJXLKOJ-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-(4-methylpiperazin-1-yl)propan-2-ol Chemical compound C1CN(C)CCN1CC(O)CN1C2=CC=C(Br)C=C2C2=CC=CC=C21 HENAKKLFJXLKOJ-UHFFFAOYSA-N 0.000 claims description 2
JSPYXAJLEQZCRS-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(1,3-thiazol-2-yl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1C1=NC=CS1 JSPYXAJLEQZCRS-UHFFFAOYSA-N 0.000 claims description 2
DIWHKVGYIDGIKS-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-(5,5-dimethyl-4h-1,3-thiazol-2-yl)piperazin-1-yl]propan-2-ol Chemical compound S1C(C)(C)CN=C1N1CCN(CC(O)CN2C3=CC=C(Br)C=C3C3=CC=CC=C32)CC1 DIWHKVGYIDGIKS-UHFFFAOYSA-N 0.000 claims description 2
WMOITZZQAXMOJV-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-[4-[[4-(difluoromethoxy)phenyl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(OC(F)F)C=C1 WMOITZZQAXMOJV-UHFFFAOYSA-N 0.000 claims description 2
WJIALCOFBWYPRK-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-carbazol-9-ylpropan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN1CCN(CC=2C=C3OCOC3=CC=2)CC1 WJIALCOFBWYPRK-UHFFFAOYSA-N 0.000 claims description 2
DKVWQSLLHZHNGQ-UHFFFAOYSA-N 1-[4-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazin-1-yl]-3-(methylamino)propan-2-ol Chemical compound C1CN(CC(O)CNC)CCN1CC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 DKVWQSLLHZHNGQ-UHFFFAOYSA-N 0.000 claims description 2
VXQCFYVSUXZUTE-UHFFFAOYSA-N 1-carbazol-9-yl-3-(4-pyridin-2-ylpiperazin-1-yl)propan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1C1=CC=CC=N1 VXQCFYVSUXZUTE-UHFFFAOYSA-N 0.000 claims description 2
ZNLKXNOLACFCII-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-(1,3-thiazol-2-yl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1C1=NC=CS1 ZNLKXNOLACFCII-UHFFFAOYSA-N 0.000 claims description 2
KYYVTZWOPPHURW-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-(5,5-dimethyl-4h-1,3-thiazol-2-yl)piperazin-1-yl]propan-2-ol Chemical compound S1C(C)(C)CN=C1N1CCN(CC(O)CN2C3=CC=CC=C3C3=CC=CC=C32)CC1 KYYVTZWOPPHURW-UHFFFAOYSA-N 0.000 claims description 2
QSOCLADLLOBEPI-UHFFFAOYSA-N 1-carbazol-9-yl-3-[4-(9h-fluoren-9-yl)piperazin-1-yl]propan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN1CCN(C2C3=CC=CC=C3C3=CC=CC=C32)CC1 QSOCLADLLOBEPI-UHFFFAOYSA-N 0.000 claims description 2
ZSEBKCBKFYTIAF-UHFFFAOYSA-N 4-[[4-(3-carbazol-9-yl-2-hydroxypropyl)piperazin-1-yl]methyl]phenol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CN(CC1)CCN1CC1=CC=C(O)C=C1 ZSEBKCBKFYTIAF-UHFFFAOYSA-N 0.000 claims description 2
JOHXYKCEQDZHOS-UHFFFAOYSA-N 9-[3-(4-benzylpiperazin-1-yl)-2-methoxypropyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(OC)CN(CC1)CCN1CC1=CC=CC=C1 JOHXYKCEQDZHOS-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
QURQMIHUXXYJIT-SFHVURJKSA-N tert-butyl 4-[(2s)-3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C[C@H](O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 QURQMIHUXXYJIT-SFHVURJKSA-N 0.000 claims description 2
MQHOXHYVAQJBEJ-UHFFFAOYSA-N tert-butyl 4-[3-(3,6-dibromocarbazol-9-yl)-2,2-difluoropropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(F)(F)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 MQHOXHYVAQJBEJ-UHFFFAOYSA-N 0.000 claims description 2
RIHAVYINBMLQHZ-UHFFFAOYSA-N tert-butyl 4-[3-(3-bromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(O)CN1C2=CC=C(Br)C=C2C2=CC=CC=C21 RIHAVYINBMLQHZ-UHFFFAOYSA-N 0.000 claims description 2
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
239000004593 Epoxy Substances 0.000 claims 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
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RBJYBNDLUSCADQ-UHFFFAOYSA-N tert-butyl 4-[2-hydroxy-3-(3-phenylcarbazol-9-yl)propyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(O)CN1C2=CC=C(C=3C=CC=CC=3)C=C2C2=CC=CC=C21 RBJYBNDLUSCADQ-UHFFFAOYSA-N 0.000 description 1
GHCUUJLJIKLYAM-UHFFFAOYSA-N tert-butyl 4-[3-(3,6-dibromocarbazol-9-yl)-2-fluoropropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(F)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 GHCUUJLJIKLYAM-UHFFFAOYSA-N 0.000 description 1
NGMFIKHHMKMCOP-UHFFFAOYSA-N tert-butyl 4-[3-(3,6-dicyanocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(O)CN1C2=CC=C(C#N)C=C2C2=CC(C#N)=CC=C21 NGMFIKHHMKMCOP-UHFFFAOYSA-N 0.000 description 1
SLWHVIIJOMYEFR-UHFFFAOYSA-N tert-butyl 4-[3-(3,6-diphenylcarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(O)CN1C2=CC=C(C=3C=CC=CC=3)C=C2C2=CC(C=3C=CC=CC=3)=CC=C21 SLWHVIIJOMYEFR-UHFFFAOYSA-N 0.000 description 1
OXXPSVLVQZXJIJ-UHFFFAOYSA-N tert-butyl 4-[3-(3-acetamidocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate Chemical compound C12=CC=CC=C2C2=CC(NC(=O)C)=CC=C2N1CC(O)CN1CCN(C(=O)OC(C)(C)C)CC1 OXXPSVLVQZXJIJ-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
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230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
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VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical class CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
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UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
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BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
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Classifications

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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system

Landscapes

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Chemical & Material Sciences (AREA)
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Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
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JP2001531827A 1999-10-18 2000-10-18 Ｂａｘ修飾物質としての９−（ピペラジニルアルキル）カルバゾール Expired - Fee Related JP5053492B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP99810944A EP1094063A1 (de)	1999-10-18	1999-10-18	9-(Piperazinylalkyl)carbazole als Bax-Modulatoren
EP99810944.1		1999-10-18
PCT/IB2000/001497 WO2001029028A1 (en)	1999-10-18	2000-10-18	9- (piperazinylalkyl) carbazoles as bax-modulators

Publications (2)

Publication Number	Publication Date
JP2003512371A JP2003512371A (ja)	2003-04-02
JP5053492B2 true JP5053492B2 (ja)	2012-10-17

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JP2001531827A Expired - Fee Related JP5053492B2 (ja)	1999-10-18	2000-10-18	Ｂａｘ修飾物質としての９−（ピペラジニルアルキル）カルバゾール

Country Status (10)

Country	Link
US (2)	US8053436B1 (de)
EP (2)	EP1094063A1 (de)
JP (1)	JP5053492B2 (de)
AT (1)	ATE397602T1 (de)
AU (1)	AU780742B2 (de)
CA (1)	CA2385456C (de)
DE (1)	DE60039125D1 (de)
ES (1)	ES2304354T3 (de)
IL (1)	IL149163A0 (de)
WO (1)	WO2001029028A1 (de)

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US9162980B2 (en)	2009-01-09	2015-10-20	Board Of Regents Of The University Of Texas System	Anti-depression compounds
US8673920B2 (en)	2009-05-06	2014-03-18	Merck Sharp & Dohme Corp.	Inhibitors of the renal outer medullary potassium channel
EP2632465B1 (de)	2010-10-27	2015-12-30	Merck Sharp & Dohme Corp.	Inhibitoren des renalen kaliumkanals der äusseren medulla
WO2012058134A1 (en)	2010-10-29	2012-05-03	Merck Sharp & Dohme Corp.	Inhibitors of the renal outer medullary potassium channel
WO2013028543A1 (en) *	2011-08-19	2013-02-28	Emory University	Bax agonist, compositions, and methods related thereto
ES2605164T3 (es)	2011-08-19	2017-03-13	Merck Sharp & Dohme Corp.	Inhibidores del canal de potasio de la médula renal externa
WO2013039802A1 (en)	2011-09-16	2013-03-21	Merck Sharp & Dohme Corp.	Inhibitors of the renal outer medullary potassium channel
US9187439B2 (en)	2011-09-21	2015-11-17	Inception Orion, Inc.	Tricyclic compounds useful as neurogenic and neuroprotective agents
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WO2014031125A1 (en) *	2012-08-24	2014-02-27	Board Of Regents Of The University Of Texas System	Pro-neurogenic compounds
WO2014085210A1 (en)	2012-11-29	2014-06-05	Merck Sharp & Dohme Corp.	Inhibitors of the renal outer medullary potassium channel
WO2014099633A2 (en)	2012-12-19	2014-06-26	Merck Sharp & Dohme Corp.	Inhibitors of the renal outer medullary potassium channel
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EP2956142B1 (de)	2013-02-18	2017-09-20	Merck Sharp & Dohme Corp.	Inhibitoren des renalen kaliumkanals der äusseren medulla
US9765074B2 (en)	2013-03-15	2017-09-19	Merck Sharp & Dohme Corp.	Inhibitors of the renal outer medullary potassium channel
US9751881B2 (en)	2013-07-31	2017-09-05	Merck Sharp & Dohme Corp.	Inhibitors of the renal outer medullary potassium channel
WO2015070237A1 (en)	2013-11-11	2015-05-14	Board Of Regents Of The University Of Texas System	Neuroprotective chemicals and methods for identifying and using same
EP3068388A4 (de)	2013-11-11	2017-04-12	Board of Regents of the University of Texas System	Nervenschützende verbindungen und verwendung davon
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1999
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US8410110B2 (en)	2013-04-02
EP1094063A1 (de)	2001-04-25
US20120040933A1 (en)	2012-02-16
EP1237887A1 (de)	2002-09-11
DE60039125D1 (de)	2008-07-17
AU780742B2 (en)	2005-04-14
WO2001029028A1 (en)	2001-04-26
CA2385456C (en)	2012-01-17
ATE397602T1 (de)	2008-06-15
CA2385456A1 (en)	2001-04-26
ES2304354T3 (es)	2008-10-16
IL149163A0 (en)	2002-11-10
JP2003512371A (ja)	2003-04-02
EP1237887B1 (de)	2008-06-04
AU7811200A (en)	2001-04-30
US8053436B1 (en)	2011-11-08

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